NDLI: Bis(4′-dibutylaminostyryl)benzene: Spectroscopic Behavior upon Protonation or Methylation

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Bis(4′-dibutylaminostyryl)benzene: Spectroscopic Behavior upon Protonation or Methylation

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Bunz, Uwe H. F. Tolosa, Juan Tolbert, Laren M. Zucchero, Anthony J.
Description	Author Affiliation: Zucchero AJ ( School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, GA 30332, USA.)
Abstract	We have investigated the UV/Vis absorption and emission of 1,4-bis(4′-dibutylaminostyryl)benzene (1) upon protonation with trifluoroacetic acid in dichloromethane and in acetonitrile. We find that 1 does not display significantly dynamic acidity in the excited state, that is, it is not a photoacid. Three protonation states of 1 were investigated, all of which, neutral, singly protonated, and bis-protonated, are fluorescent. As an isolable model for the mono-protonated species, a methylated derivative of 1 was prepared by reaction with methyl triflate. This species displays redshifted emission but similar absorption as the non-quaternized parent, 1. The strong observed emission of all three protonated states of 1 suggests that the kinetic photoacidity of 1* is low or absent. We assume that the lifetime of the excited state is too short to allow solvent reorganization and therefore we cannot make a statement on the thermodynamic photoacidity of the protonated forms of 1.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	47
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-12-07
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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